EP0178356A1
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EP
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Production of aromatic sulfonyl chlorides containing a quinonediazido group
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1984-10-18
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Granted: —
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Expires: 2004-10-18
Abstract
Abstract An aromatic sulfonic acid or its salt containing a quinonediazido group is reacted with phosgene in the prescence of a catalyst by a simplified procedure to obtain a corresponding aromatic sulfonyl chloride in high yield.
Inventors
- 👤 Yasuhiko Inoue
- 👤 Kazuhiko Hata
- 👤 Katsuhisa Masumoto
- 👤 Masaru Kamoda
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 15:59
CPC Classifications
C; C07; C07C; C07C309/00; C07C309/78; C07C309/86
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
167 words
A process for producing an aromatic sulfonyl chloride having a quinonediazido group, represented by the following general formula (II): wherein R, which may be the same or different, is a monovalent substituent selected from halogen atoms, nitro groups, and alkyl groups having from 1 to 5 carbon atoms; Ar is an aromatic organic group having a quinonediazide structure which is substituted by at least one oxy anion and at least one diazonium cation; i is an integer of from 0 to 5; and j is an integer of from 1 to 5, from a sulfonic acid or a salt thereof represented by the following general formula (I): wherein R, Ar, i and j are as defined above; and M is a hydrogen atom, a mono-, di- or trivalent metal, or an organic amino cation, characterised in that the sulfonic acid or salt thereof represented by the formula (II) is reacted with phosgene in the presence of a catalyst and in the presence or absence of a solvent.
Claim 2
Dependent Claim
167 words
A process for producing an aromatic sulfonyl chloride having a quinonediazido group, represented by the following general formula (II): wherein R, which may be the same or different, is a monovalent substituent selected from halogen atoms, nitro groups, and alkyl groups having from 1 to 5 carbon atoms; Ar is an aromatic organic group having a quinonediazide structure which is substituted by at least one oxy anion and at least one diazonium cation; i is an integer of from 0 to 5; and j is an integer of from 1 to 5, from a sulfonic acid or a salt thereof represented by the following general formula (I): wherein R, Ar, i and j are as defined above; and M is a hydrogen atom, a mono-, di- or trivalent metal, or an organic amino cation, characterised in that the sulfonic acid or salt thereof represented by the formula (II) is reacted with phosgene in the presence of a catalyst and in the presence or absence of a solvent.
Claim 3
Dependent Claim
162 words
A process as claimed in Claim 1, wherein said sulfonic acid or salt thereof of the formula (I) is an aromatic sulfonic acid or a salt thereof represented by one of the following formulae (III), (IV) or (V): wherein R 1 and R 2 , which may be the same or different, are each an aromatic fused ring residue represented by a monovalent substituent represented by -S0 3 M, or a monovalent substituent represented by -X, in which X, which may be the same or different, is a monovalent substituent selected from a hydrogen atom, a halogen atom, a nitro group, and an alkyl group having from 1 to 3 carbon atoms; and M is a hydrogen atom, a mono-, di-or trivalent metal, or an organic amino cation; and a, b, c, m, n and g are each 0 or a positive integer satisfying the relations that a+m=2, b+n=4, and c+p=4, provided that at least one -SO 3 M group is present.
Claim 4
Dependent Claim
34 words
A process as claimed in Claim 2, wherein the aromatic ring of said aromatic sulfonic acid or salt thereof of the formula (III), (IV), or (V) is a benzene ring or a naphthalene ring.
Claim 5
Dependent Claim
56 words
A process as claimed in Claim 1, 2, or 3, wherein in the formulae (I), (III), (IV), and (V), M is a hydrogen atom, a sodium atom, a potassium atom, a magnesium atom, a calcium atom, a barium atom, an aluminum atom, a trimethylammonium group, a triethylammonium group, a pyridinium group, or an N,N-dimethyl- anilinium group.
Claim 6
Dependent Claim
34 words
A process as claimed in Claim 4, wherein said sulfonic acid or salt thereof (I) is 1 ,2-benzoquinonediazidemonosulfonic acid, 1,2-naphthoquinone- diazideminosulfonic acid or 2,1-naphthoquinonediazidemonosulfonic acid, or a sodium, potassium, calcium or barium salt thereof.
Claim 7
Dependent Claim
30 words
A process as claimed in Claim 5, wherein said sulfonic acid or salt thereof (I) is 1,2-naphthoquinonediazide-5-sulfonic acid or 2,1-naphthoquinonediazide-4-sulfonic acid, or a sodium, potassium, calcium or barium salt thereof.
Claim 8
Dependent Claim
34 words
A process as claimed in any preceding Claim, wherein the amount of phosgene used is from-1 to 2 moles per mole of the sulfonic acid group in said sulfonic acid or salt thereof (I).
Claim 9
Dependent Claim
15 words
A process as claimed in any preceding Claim, wherein said catalyst is an acid amide.
Claim 10
Dependent Claim
13 words
A process as claimed in Claim 8, wherein said acid amide is N,N-dimethylformamide.
Claim 11
Dependent Claim
33 words
A process as claimed in any preceding Claim, wherein the amount of catalyst used is at least 0.01 mole per mole of the sulfonic acid group in said sulfonic acid or salt thereof(I).
Claim 12
Dependent Claim
20 words
A process as claimed in any preceding Claim, wherein said solvent contains methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane or tetrachloroethylene.
Claim 13
Dependent Claim
17 words
A process as claimed in any preceding Claim, wherein the reaction temperature is from -30°C to 100°C.
References Cited (Backward Citations)
EP0001277A1
Cited
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